DE607217C - Process for the preparation of unsaturated ketones - Google Patents

Process for the preparation of unsaturated ketones

Info

Publication number
DE607217C
DE607217C DESCH98934D DESC098934D DE607217C DE 607217 C DE607217 C DE 607217C DE SCH98934 D DESCH98934 D DE SCH98934D DE SC098934 D DESC098934 D DE SC098934D DE 607217 C DE607217 C DE 607217C
Authority
DE
Germany
Prior art keywords
preparation
unsaturated ketones
unsaturated
parts
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DESCH98934D
Other languages
German (de)
Inventor
Dr Erich Borgwardt
Dr Erwin Schwenk
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Schering Kahlbaum AG
Original Assignee
Schering Kahlbaum AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering Kahlbaum AG filed Critical Schering Kahlbaum AG
Priority to DESCH98934D priority Critical patent/DE607217C/en
Application granted granted Critical
Publication of DE607217C publication Critical patent/DE607217C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Darstellung ungesättigter Ketone Gemäß den Patenten 582 545 und 584 373 werden a, (3-ungesättigte Cycloketone in der Weise erhalten, daß man Cycloolefine der Oxydation mit Selendioxyd oder seleniger Säure mit oder ohne Lösungsmittel unterwirft.Method of Preparing Unsaturated Ketones According to the patents 582 545 and 584 373 a, (3-unsaturated cycloketones are obtained in the manner that one cycloolefins of the oxidation with selenium dioxide or selenious acid with or Subjected without solvent.

Es wurde weiterhin festgestellt, daß diese Reaktion nicht beschränkt ist auf die Verwendung von Cycloolefmen, sondern daß alle solche Stoffe benutzt werden können, in denen eine CH2-Grupp,e neben einer Doppelbindung steht. Beispielsweise seien genannt das Eugenol, bei dem die Doppelbindung und die zugehörige CH2-Gruppe in der Seitenkette eines aromatischen Ringes sich befinden, sowie die ölsäure, in der eine rein aliphatische Verbindung mit der oxydierbaren Gruppierung vorkommt.It was further found that this reaction is not limited is based on the use of cycloolefins, but that all such substances are used can be, in which a CH2 group, e is next to a double bond. For example may be mentioned the eugenol, in which the double bond and the associated CH2 group in the side chain of an aromatic ring, as well as oleic acid, in which is a purely aliphatic compound with the oxidizable group.

Beispiel i i o Teile Eugenol werden in i oo Teilen Äthylalkohol gelöst und mit einer Auflösung von 7 Teilen Selendioxyd in Alkohol nach und nach versetzt, wobei gleichzeitig unter Rühren gekocht und auf i 2o° -erhitzt wird. Nach Vollendung der Reaktion wird der Alkohol im Vakuum abdestilliert und der Rückstand hierauf mit 5 % Natronlauge, gründlich extrahiert. Beim Ans4uern erhält man das neue Keton in fester mikrokristallinischer Form. Der Schmelzpunkt der Substanz; die durch mehrfache Umfällung gereinigt ist, liegt bei 95°. Das Berizoat wird in der üblichen Weise durch Einwirkung von Benzoylchlorid auf die alkalische Lösung erhalten und schmilzt bei 117'.EXAMPLE 100 parts of eugenol are dissolved in 100 parts of ethyl alcohol and gradually mixed with a solution of 7 parts selenium dioxide in alcohol, at the same time it is cooked with stirring and heated to 120 °. After completion the reaction, the alcohol is distilled off in vacuo and the residue is then extracted thoroughly with 5% sodium hydroxide solution. The new ketone is obtained when acidifying in solid microcrystalline form. The melting point of the substance; which by multiple Reprecipitation is purified, is 95 °. The berizoat is made in the usual way obtained by the action of benzoyl chloride on the alkaline solution and melts at 117 '.

Beispiel 2 i o Teile ölsäure oder deren Ester werden in Methylalkohol gelöst und nach Zugabe von 45 Teilen seleniger Säure, in Äthylalkohol gelöst, zum Kochen erhitzt. Nach Vollendung der Reaktion wird der Äthylalkohol abdestilliert und der zurückbleibende Rückstand isoiliert. Die erhaltenen Produkte sind Gemische von Ketonen der Formel C17- H31 O # C O O H.EXAMPLE 2 10 parts of oleic acid or its esters are dissolved in methyl alcohol dissolved and after the addition of 45 parts of selenious acid, dissolved in ethyl alcohol, for Cooking heated. When the reaction is complete, the ethyl alcohol is distilled off and the residue that remains is isolated. The products obtained are mixtures of ketones of the formula C17- H31 O # C O O H.

Claims (1)

PATENTANSPRUCH: Weiterbildung des Verfahrens zur Darstellung urigesättigter Ketoverbindungen nach den Patenten 582 545 und 584 373, dadurch gekennzeichnet, daß man Selendioxyd oder selenige Säure auf ungesättigte Verbindungen einwirken läßt, welche die Gruppe C H = C H - C H2 nicht in cyclischer Bindung @enthalten.PATENT CLAIM: Further development of the method for the representation of unsaturated Keto compounds according to patents 582 545 and 584 373, characterized in that that selenium dioxide or selenious acid act on unsaturated compounds leaves which do not contain the group C H = C H - C H2 in a cyclic bond @.
DESCH98934D 1932-09-21 1932-09-21 Process for the preparation of unsaturated ketones Expired DE607217C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DESCH98934D DE607217C (en) 1932-09-21 1932-09-21 Process for the preparation of unsaturated ketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH98934D DE607217C (en) 1932-09-21 1932-09-21 Process for the preparation of unsaturated ketones

Publications (1)

Publication Number Publication Date
DE607217C true DE607217C (en) 1934-12-19

Family

ID=7446484

Family Applications (1)

Application Number Title Priority Date Filing Date
DESCH98934D Expired DE607217C (en) 1932-09-21 1932-09-21 Process for the preparation of unsaturated ketones

Country Status (1)

Country Link
DE (1) DE607217C (en)

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